Pyrimidines

Application of 56844-12-3 , The common heterocyclic compound, 56844-12-3, name is 6-Bromo-4-chlorothieno[2,3-d]pyrimidine, molecular formula is C6H2BrClN2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A stirred solution of 6-bromo-4-chlorothieno[2,3-d]pyrimidine (4.0g, 0.016mol) in anhydrous tetrahydrofuran (100ml) was cooled in a dry-ice/acetone bath and treated, under a nitrogen atmosphere, with lithium diisopropylamide (1.8M solution in tetrahydrofuran, 9.0ml, 0.016mol) over about 20 minutes. The resultant dark solution was stirred in the cold for 1 hour and then treated with a mixture of water (5ml) and tetrahydrofuran (20ml) over about 20 minutes. The mixture was then allowed to warm up to about 0C before being poured into water (250ml) and extracted with dichloromethane (SxlOOml). The combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to give the crude product. Purification by flashchromatography (silica) eluting with dichloromethane gave 5-bromo-4-chlorothieno[2,3-cQpyrimidine as a pale brown solid (3.8g).

The synthetic route of 56844-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENTION DISCOVERY LIMITED; WO2004/111057; (2004); A1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.14080-23-0, name is 2-Cyanopyrimidine, molecular formula is C5H3N3, molecular weight is 105.0974, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Cyanopyrimidine

To a stirring solution of 2-cyanopyrimidine (2.0 g, 19.0 mmol) in methanol (50 mL) were added 10%Pd/C (300 mg), 12 N HCI (1.5 mL) under 2 atmosphere. The reaction mixture was stirred under atmosphere (balloon pressure) at RT for 3 h. After consumption of the starting material (by TLC), the reaction mixture was filtered through a pad of celite and the pad was washed with methanol. Obtained filtrate was concentrated under reduced pressure to afford crude compound which was triturated with diethyl ether to obtained compound 2S-Y (1.2 g, 44%) as white solid. 1H-NMR: (500 MHz, DMSO-i): delta 8.87 (d, J= 5.0 Hz, 2H), 8.69 (br s, 2H), 7.52 (t, J= 5.0 Hz, 1H), 4.24 (s, 2H); Mass (ESI): 1 10.3 [M++l]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14080-23-0, 2-Cyanopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NAUREX, INC.; LOWE, John, A., III; KHAN, M., Amin; WO2014/120783; (2014); A1;,
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Synthetic Route of 51421-99-9 , The common heterocyclic compound, 51421-99-9, name is 4-Chloro-2-methoxypyrimidine, molecular formula is C5H5ClN2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

159.2 2-Chloro-5-(2-methoxyDyrimidine-4-carbonyl)benzoic acid methyl esterA 60% suspension of NaH in mineral oil (51 mg) was added to a solution of 4-chloro-2- methoxypyrimidine (123 mg), intermediate 159.1 (170 mg) and dimethylimidazolium iodide (96 mg) in dioxane (35 mL). The reaction mixture was heated to reflux for 4h30 and ON at RT. It was diluted with water and extracted with EtOAc. The organic phase was dried over MgS04 and concentrated in vacuo. The crude was purified by CC (Hept/EtOAc 1/0 to 7/3) to give 49 mg of the titled compound as a light yellow solid.LC-MS (B): tR = 0.77 min; [M+H]+: 307.19

The synthetic route of 51421-99-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HILPERT, Kurt; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; WO2012/114268; (2012); A1;,
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Related Products of 145783-15-9, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.145783-15-9, name is 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, molecular formula is C7H9Cl2N3S, molecular weight is 238.14, as common compound, the synthetic route is as follows.

4,6-Dichloro-2-(propylthio)pyrimidin-5-amine (0.5 g, 2.1 mmol) was dissolved in methanol (2 mL) and supplemented with 2,2,2-trifluoroethanamine (625.0 mg, 6.3 mmol). The reaction mixture was introduced in a sealed vessel and heated at 100C for 24 h. After concentration of the reaction mixture to dryness under vacuum, the residue was purified by silica gel column chromatography. Yield: 76%.Melting point: 107-109C.*H NMR (DMSO -d6) d 0.95 (t, J=7.4 Hz, 3H, SCH2CH2C/ ,), 1.63 (h, J=7.3 Hz, 2H, SCH2CH2CH3),2.95 (t, J=7.2 Hz, 2H, SCH2CH2CH3), 4.29 (m, 2H, NHCH2CF3), 4.95 (s, 2H, NH2), 7.53 (s, 1H, NHCH2CF3).13C NM R (DMSO-c/g) d 13.2 (SCH2CH2CH3), 22.6 (SCH2CH2CH3), 32.1 (SCH2CH2CH3), 41.2 (q, J=33 Hz, NHCH2CF3), 120.5 (C-5), 122.7-126.0 (m, NHCH2CF3), 138.8 (C-6), 151.9 (C-4), 154.8 (C-2).

Statistics shows that 145783-15-9 is playing an increasingly important role. we look forward to future research findings about 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine.

Reference:
Patent; UNIVERSITE DE LIEGE; LANCELLOTTI, Patrizio; OURY, Cecile; PIROTTE, Bernard; (140 pag.)WO2019/158655; (2019); A1;,
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Synthetic Route of 29274-24-6, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below.

A mixture of A-7 (300.0 mg, 1.95 mmol), 1-[4-(4,4,5,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)phenyllcyclopropanecarbonitrile (629.81 mg, 2.34 mmol), Pd(t-Bu3P)2(149.48 mg, 292.50 pmol) and K3P04 (827.85 mg, 3.90 mmol) in dioxane (10 mL) and H20(3.90 mL) was stirred at 80 C for 16 hours. The mixture was concentrated to give the crudeproduct, which was purified by silica gel (EtOAc in PE = 10% to 20% to 100%) to afford A-il(600.00 mg, 1.86 mmol) as a solid. ?H NMR (400MHz, DMSO-d6) 0119.19 (dd, 1H), 8.30 – 8.17(m, 3H), 7.66 (d, 1H), 7.49 (dd, 2H), 6.76 (d, 1H), 1.91 – 1.80 (m, 2H), 1.68 – 1.58 (m, 2H).LCMS R = 0.762 mm in 1.5 mins chromatography, MS ESI calcd. for C,6H,3N4 [M+H1 261.1, found 260.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew Mark; MARRON, Brian Edward; (168 pag.)WO2018/98500; (2018); A1;,
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Synthetic Route of 26032-72-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 26032-72-4 as follows.

The following compounds presented in Examples 52-92 w^ere prepared in accordance with Scheme 6, by a procedure analogous to that disclosed in Examples 39 and 48, using starting materials with the appropriate substitution.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26032-72-4, its application will become more common.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; KALLEDA, Srinivas; PADAKANTI, Srinivas; KUMAR SWAMY, Nalivela; YELESWARAPU, Koteswar, Rao; ALEXANDER, Christopher, W.; KHANNA, Ish, Kumar; IQBAL, Javed; PILLARISETTI, Sivaram; PAL, Manojit; BARANGE, Deepak; WO2006/34473; (2006); A2;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.10320-42-0, name is 2-Chloro-5-nitropyrimidine, molecular formula is C4H2ClN3O2, molecular weight is 159.5306, as common compound, the synthetic route is as follows.Safety of 2-Chloro-5-nitropyrimidine

Intermediate 1895-nitro-2-[(3,3 -trimethyl-2,3-dihvdro-l-benzofuran-4-yl)oxylpyrimidine3,3,7-Trimethyl-2,3-dihydro-l-benzofuran-4-ol (Intermediate 184, 178 mg, 1.0 mmol) and 2-chloro-5- nitropyrimidine (191.5 mg, 1.2 mmol) were dissolved in CH3CN (3.0 mL) and K2C03 (345.5 mg, 2.5 mmol) was added. The resulting suspension was heated to 40°C and stirred for 1 hour. The reaction mixture was then diluted with water (50 mL) and ethyl acetate (50 mL), The organic phase wascollected, washed with brine (50 mL) and dried over Na2S04. The residue was purified by flash chromatography on silica gel using cyclohexane/ ethyl acetate 97:3 as eluents affording the title compound (243 mg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10320-42-0, 2-Chloro-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; AUTIFONY THERAPEUTICS LIMITED; ALVARO, Giuseppe; DAMBRUOSO, Paolo; MARASCO, Agostino; TOMMASI, Simona; DECOR, Anne; LARGE, Charles; WO2012/76877; (2012); A1;,
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Electric Literature of 32779-36-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 32779-36-5, name is 5-Bromo-2-chloropyrimidine. A new synthetic method of this compound is introduced below.

5-Bromo-2-phenoxypyrimidine (intermediate AU) A mixture of 5-bromo-2-chloropyrimidine (5.00 g, 0.0259 mol), phenol (3.16 g, 0.0336 mol), dibenzo-18-Crown-6 (0.47 g, 0.0013 mol) and ground potassium hydroxide (3.51 g, 0.0626 mol) in toluene (75 ml) was heated at reflux for 5 hours with azeotropic removal of water. The mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure. The residue was partitioned between water and chloroform. The layers were separated and the aqueous phase was extracted with chloroform three times. The combined organic layers were dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography on silica using n-heptane/ethyl acetate (98:2) as an eluent to give 5-bromo-2-phenoxy-pyrimidine as a white solid (3.55 g, 0.0141 mol): 1H NMR (DMSO-d6, 400 MHz) 8.80 (s, 2H), 7.45 (t, 2H), 7.27 (t, 1H), 7.22 (d 2H); TLC (n-heptane/ethyl acetate=95:5) Rf 0.20.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,32779-36-5, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6921763; (2005); B2;,
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Synthetic Route of 153435-63-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine. A new synthetic method of this compound is introduced below.

A solution of the product from step 1 (1.74 g, 7.87 mmol), 2-20 (tributylstannyl)pyrimidine ( 4.36 g, 11.81 mmol), CsF ( 4.78 g, 31.5 mmol), and copper() iodide(0.450 g, 2.36 mmol) in DMF (16 mL) in a pressure vessel was sparged with nitrogen andtreated with Pd(PPh3)4 (0.455 g, 0.394 mmol). The mixture was sealed and heated at 120 ocovernight. The cooled reaction mixture was partitioned between EtOAc and water and filteredthrough celite. The organic layer was washed with saturated aqueous sodium bicarbonate and25 brine, dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silicagel chromatography (0-30% EtOAc in hexanes), to provide the title compound as a yellow solid.LRMS m/z (M+H) 221.2 found, 221.1 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; MENG, Na; YU, Tingting; WO2015/18029; (2015); A1;,
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Application of 153435-63-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine. A new synthetic method of this compound is introduced below.

A solution of 2-bromo-3-thiophene carboxylic acid (3.35 g, 16.2 mmol) in methanol (50 mL) was cooled to 0 C and saturated with gaseous HC1. The solution was heated to 60 C overnight, then concentrated in vacuo. The residue was redissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and concentrated, providing methyl 2-bromothiophene-3-carboxylate as yellow oil. LRMS m/z (M+H) 221.1 found, 221.0 required. A solution of methyl 2-bromothiophene-3-carboxylate (1.74 g, 7.87 mmol), 2-(tributylstannyl)pyrimidine (4.36 g, 11.81 mmol), cesium fluoride (4.78 g, 31.5 mmol), and copper(I) iodide (0.450 g, 2.36 mmol) in DMF (16 mL) in a pressure vessel was purged subsurface with nitrogen and treated with palladium tetrakis (0.455 g, 0.394 mmol). The mixture was sealed and heated at 120 C overnight. The reaction was partitioned between ethyl acetate and water and filtered through celite. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel gradient chromatography (0-30% ethyl acetate in hexanes), providing methyl 2- (pyrimidin-2-yl)thiophene-3-carboxylate as a yellow solid. LRMS m/z (M+H) 221.2 found, 221.1 required. A solution of methyl 2-(pyrimidin-2-yl)thiophene-3-carboxylate (0.695 g, 3.16 mmol) and potassium trimethylsilanolate (0.506 g, 3.94 mmol) in THF (16 mL) was stirred at RT overnight, then diluted with ether and filtered through a glass frit. The solids were washed with ether, and the filtrate was concentrated, providing the title compound as a beige solid. LRMS m/z (M+H) 207.3 found, 207.1 required.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153435-63-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2015/95442; (2015); A1;,
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